Synthetic lubricating agents and hydraulic liquids



3,250,708 SYNTHETIC LUBRICATING AGENTS AND HYDRAULIC LIQUIDS JoachimDazzi, Riehen, and Ernst Keller, Binningen, near Basel, Switzerland,assignors to J. R. Geigy A.G.,

This application is a continuation-in-part application of our pendingpatent applications Serial Nos. 208,104 (now abandoned); 208,105 (nowabandoned); 208,106 (now abandoned), all three filed on July 6, 1962;Serial No. 249,120, filed on January 3, 1963; and Serial No. 357,851(now abandoned), filed on March 11, 1964. I

The present invention concerns the use of certain N-substitutedmelamines as synthetic lubricating agents and/or as hydraulic liquids,as Well as compositions which, in addition to the melamine derivativesuseable according to the invention, also contain other usual min eral orsynthetic liquids as well as the usual antioxidants, thickeners, agentslowering the congealing point, high pressure additives and/ oranticorrosives. The invention also concerns processes for thelubrication or hydraulic propulsion of machines or parts thereof withthe new compositions containing the aforesaid melamine derivatives whichcan be used as lubricating agents and/ or hydraulic fluids.

Very high demands with regard to heat stability are made of syntheticlubricating agents and hydraulic fluids such as are necessary, forexample, in gas turbine engines especially for airplanes or the modernhigh temperature equipment used in the mechanical and electricalindust-ries.

For use in gas turbine engines especially for airplanes, syntheticlubricating agents must primarily fulfill the following conditions:

(1) They must be capable of forming a lubricating film on the mostvarious metals;

(2) They must be only slightly volatile andhave extensive stability toheat;

(3) They should not have a corrosive action and, above all, they shouldnot form acid decomposition products;

(4) They should retain their lubricating properties over as wide atemperature range as possible, i.e., their viscosity should be as littledependent as possible on temperature;

(5) They should have, in addition to these properties,

on the one hand as low a solidification point as possible and on theother as high a boiling point as possible.

It is difiicult to find substances which fulfill these.

demands to such an extent that they can be employed, for example, aslubricants for gas turbine engines. The usual lubricants do not fulfillthe demands of modern motors, in particular of the aforesaid type ofairplane engines, those of an ester basis because of their volatilityand insufficient heat stability and those of a hydrocarbon basis becauseof their volatility, their solidification point and the dependence oftheir viscosity on temperature, referred to conventionally as ASTM slopeand defined in detail further below.

It has now surprisingly been found that certain melamines suitablysubstituted at the nitrogen atom of the amino groups have the propertiesrequired above and thus can be used as hydraulic fluids when highdemands are made and as synthetic lubricants for a particularly widerange of temperatures.

United States Patent 0 3,250,708 Patented May 10, 1966 According to afirst aspect of this invention, melamines suitable for use in the methodand compositions according to the invention are of the formula wherein Ris a lower alkyl group with from 4 to 6 carbon atoms.

More particularly, the melamine derivatives of the above Formula I inwhich R is either a butyl radical or a hexyl radical are of commercialinterest.

The hexa-N-substituted melamines used according to this aspect of theinvention are easily produced by reacting in successive steps, by knownmethods, the three chlorine atoms of cyanuric chloride with primary orsecondary organic amines.

In the first and/ or second step, less easily reacting amines arereacted and in the third step those which react easily are reacted. Thereaction is performed advanta-' geously in inert organic solvents anddiluents such as low aliphatic ketones, aliphatic or alicyclic etherssuch as dibutyl ether, tetrahydrofuran or dioxan, or aromatichydrocarbons or halogenated hydrocarbons such as benzene, toluene,xylene or dichlorobenzene in the presence of acid binding agents atsuitable temperatures. Examples of acid binding agents are the alkalimetal salts of lower fatty acids such as sodium acetate, also those ofweaker polybasic acids such as sodium or potassium carbonate,

sodium or potassium bicarbonate and, in suitable amount and form, alsoalkali hydroxides as well as tertiary nitrogen bases such astriethylamine, triethanolamine, pyridine,

etc. The first chlorine atom of the cyanuric chloride is reactedadvantageously at lower temperatures up to 15 C., the second chlorineatom is reacted at medium temperatures up to 60 C. and the thirdchlorine atom is reacted, if necessary, at higher temperatures, anexcess of the amine being used advantageously as acid binding agent. 1

Aliphatic amines which can be used are the primary and secondary aminescontaining normal and/ or branche chain alkyl groups of 4 to 6 carbonatoms.

The crude hexa-N-substituted melamines used accord- I ing'to theinvention may contain mixtures of primary, secondary and tertiaryamines. Due to their great stability to heat, they can easily beobtained in pure form by distillation. The melamine derivatives can alsobe purified by extraction with a selective solvent such as acetic acid,by treatment with a bleaching earth such as Tonsil AC or an absorptionearth such as Celite PC or with an ion-exchanger such as Amberlite IR120.

The hexa-N-substituted melamines used according to this aspect of theinvention are slightly volatile oils or are of a fatty or wax-likeconsistency and they are distinguished by high thermostability as theydecompose only I G for airplane engines, they form practically no aciddecomposition products.

In addition, the flash point of the melamines useable according to thisaspect of the invention is favorable. It was determined according to theASTM designation: D 9358T (The American Society for Testing Materials,1915 Race St., Philadelphia 3, Pa).

According to a second aspect of this invention, melamines usableaccording to the invention are compounds of the formula wherein X is adi-(lower alkyl)-arnino group in which each alkyl radical has from 1 to4 carbon atoms,

Y is a di-(lower alkyD-amino group in which each alkyl radical has from1 to 4 carbon atoms,

R is hydrogen or alkyl of maximally 14 carbon atoms,

R is an alkyl group of at least 6 and maximally 18 carbon atoms or acyclohexyl group, the sum of the carbon atoms of R and R being at least8 and not more than 28,

and R and R taken together with the nitrogen atom to which they arelinked represent either piperidinoor hexamethyleneimino.

Very interesting as lubricants because of their good ASTM slope which isbelow 0.8, are the compounds of the above Formula II in which there area total of five alkyl substituents at the three amino-nitrogen atoms,one of which substituents is an alkyl group with 18 carbon atoms.

Another subclass of compounds which are particularly interesting in viewof their good lubricant properties, (ASTM slope in the range of about0.7 and lower, and weight loss at 380 C. of less than 6%) are thosecompounds of the above Formula II in which there are a total of sixsubstituent alkyl groups at the three aminonitrogen atoms, and whereinone of these alkyl groups has from 12 to 18 carbon atoms.

This aspect of the invention further relates to a method of lubricatinga substrate with a compound of the above Formula II, and to compositionswhich contain the aforesaid compounds as essential ingredients.

Apart from substituted, particularly alkyl-substituted amino groups, thenitrogen substituents of melamines usable according to this aspect ofthe invention must not contain any functional groups. In particular theycontain no acid, salt-forming susbtituents or any which can beconvertedinto such; for example, they contain neither sulfonic acid groups norcarboxyl, sulfonic acid ester, carboxylic acid ester, sul-famyl,carbamyl nor cyano groups.

If two substituents of the same nitrogen atom are bound in ring formthen they form, for example, the pyrrolidine, piperidine, morpholine,hexamethyleneimine or N-alkylpiperazine ring.

The N,N,N"-substituted melamines according to this second aspect of theinvention are easily produced in an analogous manner as described in thefirst aspect of this invention, but using the equivalent aliphaticamines to produce the desired compounds.

Aliphatic amines which can be used for this aspect of the invention are,for example, primaryand secondary amines containing normal and/orbranched chain alkyl groups of 1 to 18 carbon atoms, or alkoxyalkylgroups of 3 to 20 carbon atoms, or aminoalkyl groups havingadvantageously a tertiary amino group, e.g., a dialkylamino,diaralkylamino, dicycloalkylamino, alltylaralkylamino, alkylarylamino,polymethyleneimino, morpholino or N'-alkylpiperidino group. As alicyclicamines can be used, for example, cyclopentylamine, cyclohexylamine, andcycloheptyl-amine and dihydroabietinylamine; examples of secondaryamines of this series are the corresponding bis-alicyclic amines or alsosecondary alkylcycloalkyl, aralkylcycloalkyl or phenylcycloalkyl amines.

The crude N,N',N"-substituted melamines according to the second aspectof the invention can contain mixtures of primary, secondary and tertiaryamines which must be removed by purification in the same manner asdescribed in the first aspect of this invention, supra.

The N,N',N"-substituted melamines used according to this aspect of theinvention are also slightly volatile oils or are of a fatty or wax-likeconsistency and they are also distinguished by similar excellentqualities as those exhibited by the compounds according to the firstaspect of the invention.

They also have the advantage that even under extreme test conditionssuch as are required for lubricants for gas turbine engines ofairplanes, they form practically no acid decomposition products. Thus,for example the volatile compounds formed I from2-diethylamino-4-dibutylamino-S-dodecylamino-1,3,5-triazine (comparecompound No. l in the following Table III), and also the residue have anacid value of only 1 mg. KOH/g. or 0.7 mg. KOH/ g. respectively after 6hours exposure to a temperature of 380 C., i.e., both the volatilecompounds as well as the residue formed from compound No. l of Table IIIare neutral for all practical purposes after several hours exposure toheat Whereas the volatile substances formed from tirimethylolpropanetripelargonate under the same conditions have an acid value of 117.3 mg.KOH/ g.

In addition, the flash point of the melamin-es usable according to thisaspect of the invention is also favorable. It was determined accordingto the ASTM designation: D 93-58 T. In the case of compound No. 1 ofTable III mentioned above, it is above 300 C. and is thus higher thanthat of the sebacates of alkanols, now in commercial use.

Also the density of the melamines usable according to this aspect of theinvention is favorable, for example that of compound N0. 1 in thefollowing Table III is only about 0.88 and that of compound No. 16 inthe same table is only 0.85. The densities of the conventionallubricants of an ester basis are higher.

According to a third aspect of the invention melamines usable accordingto the invention are compounds of the formula wherein X is a di-(loweralkyl)-amino group in which each alkyl radical has from 2 to 4 carbonatoms,

Y is a di-(lower alkyD-amino group in which each alkyl radical has from2 to 4 carbon atoms,

R, is hydrogen or lower alkyl of maximally 4 carbon atoms,

R' is benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12 carbonatoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atoms, orphenoxyphenyl'.

Very interesting as lubricants because of their good ASTM slope which isbelow 0.8 are the compounds of the above Formula III in which there area total of four alkyl suband high heat resistance expressed by a-weightloss at up to 380 C. of less than 6%) are those compounds of the aboveFormula III in which these are a total of five substituent alkyl groupsand one aromatic group at the three amino nitrogen atoms and saidaromatic group is preferably a phenyl group.

This third aspect of the invention further relates to a method oflubricating a substrate with a compound of the above Formula HI and tocompositions which contain the aforesaid compounds as essentialingredients.

Apart from substituted, particularly aryland alkylsubstituted aminogroups, the nitrogen substituents of melamines usable according to thisaspect of the invention must not contain any functional groups. Inparticular they contain no acid, salt-forming substituents or any whichcan be converted into such; for example, they contain neither sulfonic.acid groups nor carboxyl, sulfonic acid ester, carboxylic acid ester,sulfamyl, carbamyl nor cyano groups.

The N,N',N"-substituted melamines used according to this aspect 'of theinvention, are easily produced in an analogous manner as described inthe first aspect of this invention, but using the equivalent aliphaticamines to produce the desired compounds.

Aliphatic amines which can be used for this aspect of the invention are,for example, primary and secondary amines containing normal and/orbranched chain alkyl groups of 1 to 6 carbon atoms, or alkoxyalkylgroups of 3 to 1 2 carbon atoms, or aminoalkyl groups havingadvantageously a tertiary amino group, e.g. a dialkylamino,diaralkylamino, dicycloalkylamino, alkylaralkylamino, alkylarylamino,polymethyleneimino, morpholino or N'- alkylpiperazino group.

Examples of primary aromatic amines are aniline, chloroor bromo-aniline,alkylanilines such as toluidines, xylidines, tert-butyl or tert-amylanilines, aminotetrahydronaphthalenes, aminodiphenyls,aminodiphenylalkanes, aminodiphenylamines, aminodiphenyl ethers,aminodiphenylthioethers and secondary amines of this series such ascompounds which have been alkylated, aralkylated or alicyclicallysubstituted at the amino nitrogen atom.

The crude N,N',N"-substitutedmelamines according to this third aspect ofthe invention can contain mixtures of primary, secondary and tertiaryamines. Because of their great stability to heat, they can easily beobtained in pure form by distillation. The melamine derivatives can alsobe purified by extraction with a selective solvent such as acetic acid,by treatment with a bleaching earth such as Tonsil AC or an adsorptionearth such as Celite PC or with an ion-exchanger such as Amberlite IR120.

The N,N,N-substituted melamines used according to this aspect of theinvention are also slightly volatile oils or are of a fatty or wax-likeconsistency and they are distinguished by high thermostability as theydecompose only at temperatures above 380 C. In this respect they havethe advantage over the best products used up to new for this purpose,namely the triesters of higher fatty acids with trimethylolpropane;these cannot be used at temperatures above 320 C. In addition, thelubricants and hydraulic fluids according to this aspect of theinvention are more stable to hydrolysis than lubricants of an esterbasis which have been used up to now.

They also have the advantage that even under extreme test conditionssuch as are required for lubricants used in gas turbine engines orairplanes, they form practically no acid decomposition products. Thus,for example, the volatile compounds formed from 2,4-bis-dibutylamino-6-p-phenoxyphenyl-1,3,5-triazine (compare compound No. 3

in the following Table VI), and also the residue have an acid value ofonly 1 mg. KOH/g. or 0.7 mg. KOH/g. respectively after 6 hours exposureto a temperature of 380 C., i.e., both the volatile compounds as well asthe residue formed from compound No. 3 of Table VI are neutral for allpractical purposes after several-hours exposure to heat whereas thevolatile substances formed from trimethylolpropane tripelargonateunder'the same conditions have an acid value of 117.3 mg. KOI-I/ g.

In addition, the flash point of the melamine usable according to thisaspect of the invention is favorable. It was determined according to theASTM designation: D 93-58 T. In case of compound 3 of Table VI mentionedabove, it is 300 C. and is thus higher than that of the sebaceates ofalkanols now in commercial use.

The melamines according to the three aspects of this invention aredistinguished over the previously known substances recommended aslubricants for turbine engines such as, e.g., the ort-ho-phosphoric acidesters of organic hydroxyl compounds, by their much slighter corrosiveaction; they are distinguished over the esters of higher polycarboxylicacids with polyalcohols by their lesser swelling action on syntheticmaterials such as, e.g. on high molecular copolymers from b-utadiene andacrylonitrile (e.g. Hycar 38 made by Messrs. Goodrich in Akron, Ohio,U.S.A.); and they are distinguished over esters from pentaerythrite andmonocarboxylic acids of medium chain length by considerably lessseparation of resini-fication and carbonization products. They are alsodistinguished over all these known lubricants in that, in additiontohaving good properties at low temperatures, they are very stableparticularly at high temperatures. 7 In addition, they are distinguishedover the silicone oils, some of which are also thermostable, by theirbetter lubricating properties and they are distinguished over polyphenylethers by their lower solidification point and, therefore, their greaterusefulness in the modern engines now in use. good stability to acid andalkali of the melmine derivatives used according to the invention isalso remarkable. In the liquid state, these melamine derivatives havemedium to high viscosity; their great advantage lies in the fact thatthis viscosity is only slightly dependent .on temperature.

The melamines useable according to the invention can be employed aslubricants in many Ways. Properties desirable for a particular purposecan also be attained by the production of suitable mixtures of thesemelamines.

Thus, the melamines useable according to the invention are suitable forthe lubrication of hard surfaces because, on contact with thesesurfaces, they form very adhesive surface films, e.g., they are suitablefor lubricating the surface of metals as-well as alloys thereof, thesurfaces of silicates such as, e.g., glasses as well as of othermaterials needing lubrication such as, e.g., rubber Washers.

The N,N',N"-substituted melamines useable according to the invention canbe employed alone or they can also contain additives. Thus, when theyare to be used at temperatures of over C., to make use of theirfavorable stability to .heat they are mixed advantageously withanti-oxidants in order to hinder the auto-oxidation which sets in abovethis temperature. The amount'of antioxidant is about 0.01 to 5% of themelamine. the amines which can be used as antioxidants, generally thesecondary monoamines are particularly valuable and of these especiallythe diarylamines with homocyclic and heterocyclic aromatic radicals aswell as the aromatic diamines the substituents of which are preferablysecondary amino substituents'occupying either the orthoor, preferably,the para-position.

Examples of homocyclic and heterocyclic aromatic diaryl amines which canbe used as antioxidants are diphenylamines, phenylnaphthylamines,phenylacenaphthenylamines; 4,4 dinaphthylaminodiphe'nyl; thiazolyl-(2)-naphthylamines; examples of aromatic diamines are N,N" diphenyl pphenylenediamine, N,N'-dioctyl-pphenylenediamine, N,N' dicyclohexyl pphenylenediamine, N-sec-butyl-N'-phenyl-p-phenylenediamine, N,N'-bis-('y-aminopropyl)-p-phenylenediamine.

Of the hydroxyl-substituted aromates which are especially employed asantioxidants at not too high temperatures (i.e., below ZOO-300 C.depending on type The very.

2,4-dimethyl-6-tert-butylphenol,

2,6-di-tert-butyl-4-ethylphenol,

2,6bisl'-methylcyclohexyl) -4-methylphcnol,

2,6-di-tert-butyl-4-dimethy]-aminomethyl phenol,

2,2'-methylene-bis- 4-methyl-6-tert-butyl phenol) 2,2-thio-bis-(4-methyl-6-tert-butyl-phenol4,4-dihydroxy-2,2'-dimethyl-5,5'-di-tert-butyl-diphenyl sulphide anddiphenyl disulphide,

2,6-bis- (2'-hyd roxy-3 '-tert-butyl-5 '-methylbenzyl 4-methylphenol)1,1,3 tris- (4'-hydroxy-5 -tert-butyl-2'-methylphenyl) butane,

derivatives of polynuclear phenols such asZ-tert-butyl-l-hydroxyn,aphthalene, 4,6-di-tert-butyl-S-hydroxyindane,S-hydroxyacenaphthene,

polyvalent phenols and derivatives thereof: butyl pyrocatechol, octylgallate, hydroquinone, butylhydroxy anisole, hydroquinone monobenzylether.

Of the aminohydroxyaryl compounds useable as antioxidants thosederivatives in which the amino and hydroxyl groups are in p-position toeach other are particularly suitable. Examples are:p-hyroxy-diphenylamine, p-hydroxyoctyl aniline,p-hydroxy-N-v-aminopropyl aniline.

Of the heterocyclic compounds, which can be used as antioxidants thecyclic imides are the best known; in addition, however, alsoheterocyclic compounds having no nitrogen can be employed insofar asthey are not included in the class of heterocyclic amines. Examples are:phenothiazine, 6-methoxyor 6-ethoxyor 6-ethylamino-2,2,4-trimethyl-1,2-dihydroquinoline or telomers thereof, 3hydroxy 7,8-benzo-1,2,3,4-tetrahydro-' quinoline or tocopherol.

'Didodecyl selenide may also be used as antioxidant.

In addition, the N,N',N"substituted melamines useable according to theinvention can also contain high pressure additives such as phosphites,phosphates, sulfonated oil, etc., barium or calcium mahagony sulfonates,anti-corrosives such as 'sarcosines or benzotriaz-oles, said highpressure additives and anti-corrosives preferably being added in amountsof at least 0.01% based on the weight of the lubricant composition,agents lowering the solidification point and, optionally, alsoanti-foaming agents such as the ones based on silicones and also poly-(lower alkyl substituted hexyl methacrylate), in amounts of about 0.1 or1% and higher up to about of the weight of the lubricant composition.Anti-corrosives are added, preferably in amounts of 0.01 to 2% by weightof the melamine lubricant composition.

In addition, the invention also embraces lubricating greases made fromthe melamine derivatives used according thereto by the addition of theusual thickeners. Examples of such thickeners are metal soaps,bentonites, phthalocyanines, violanthrones, etc. Such additives arepreferably present in the lubricant compositions according to theinvention in amounts of from 10 to 45% based on the total weight of thecomposition.

The new synthetic lubricants can also be mixed with other lubricants,for example, with highly purified mineral oilfractions or with theso-called synthetic ester lubricants, i.e., esters of from 18 to 50carbon atoms,

.(a) Those of fatty acids with alkane-triand tetraols containing from 4to 10 carbon atoms, and containing not more than one oxygen atomattached to each carbon atom, such as w-tri-methylol alkanes,

(b) those of alkanedicarboxylic acids containing 4 to 14 carbon atomswith alkanols, and

(0) complex esters comprising the neutral esterification products of theabove-defined polyhydric alcohols such as trimethylolpropane andpentaerythritol with a mixture of alkanolic acids as defined above, withthe molar ratio of the polyhydric alcohol and the alkanedicarboxylicacid ranging from 4: 1 to 1.33:1; and further with esters ofortho-silicic acid with 2-ethylhexanol, and with silicones or lubricantscontaining organic phosphorus compounds.

These additives can be used in any ratio advisable for the purposeintended in correspondence with the miscibility diagram of the twocomponents. Preferred is a content of 5 to and preferably 10 to 90%, byweight of the lubricant compounds defined in Formulas I, II and IIIabove, the balance consisting of one of the abovementioned conventionallubricants.

The following examples illustrate the particular suitability of theN,N',N"-substituted melamines according to the invention for use assynthetic lubricants, as hydraulic fluids as well as oils for turbineengines. Measurements are given therein according to the metric systemand the temperatures are in degrees centigrade. Pressures are given intorr (mm. Hg).

Example 1.2,4,6-tris-dibutylamino-s-triazine H O 41TIC 4H1:

A mixture consisting of 110.8 parts of2.,4-bis-dibutylamino-6-chloro-s-triazine (B.P. 162 under 0.1 torr; 111.5071), 77.5 parts of dibutylamine and 12 parts of pulverized sodiumhydroxide are stirred for 3 hours at and then further heated and stirredfor 8 hours at The mixture is then filtered, the filtrate is washed withwater and fractionally distilled. 118 parts of a colorless oil areobtained which passes over at 196499 under 0.05 torr. Refraction index21 1.4948; yield: 85.6% of the theoretical.

Analysis.C H N M.W. 462; calculated: C 70.0 percent, H 11.70 percent, N18.20 percent. Found: C 70.10 percent, H 11.69 percent, N 18.33 percent.

This melamine derivative is a viscous liquid which is very slightlyvolatile and very thermostable. Its viscosity depends relativelyslightly on the temperature so that it is a very valuable turbine oil.

If, instead of 2,4-bis-dibutyl-amino-6-chloro-s-triazine anddibutylamine, equimolar amounts of2,4,-bis-dihexylamino-6-chloro-s-triazine and hihexylamine respectivelyare used, then 2,4,6-tris-dihexylamino-1,3,S-triazine is obtained in ananalogous manner.

Yield: 98.5% of the theoretical. 0.03 torr.

Refraction index 12 1.4890.

Analysis.C H N M.W. 630; calculated: C 74.50 percent, H 12.10 percent, N13.32 percent. Found: C 73.94 percent, H 12.32 percent, N 13.50 percent.

Example 2 50 parts of 2,4,6-tris-dihexylamino-1,3,5-triazine having aviscosity of 13.83 centistokes at 98.8 and 50 parts of a highly purifiedmineral oil (viscosity SAE 10) are stirred together. The mixture has thegood lubricating prop- B.P. 220 under erties of the components and theviscosity of the mixture is only 8.92 centistokes at 98.8.

The application range of the melamine compound used is considerablybroadened by this reduction of the viscosity in that, for example, themixture can-be used, e.g., as

power transmitting agent in parts of machines which are' temporarilyexposed to temperatures which are lower than usual working temperatures.Under such condi- Example 3 8 parts of copper phthalocyanine (IrgaplastBrilliant Blue BLP, Geigy Co. Ltd., Manchester, England), 4 parts of2,4,6-tris-dibutylamino-1,3,5-triazine and 40 parts by volume of benzeneare stirred rapidly for 15 minutes in an Ultraturax mixing apparatus(made by Janke & Kunkel, Stautl'en, Baden, Germany). Another 20 parts of2,4,6-tris-dibutylamino-1,3,5-triazine are then added and the whole isstirred rapidly for another 45 minutes.

The homogeneous mass so obtained is worked on a glass surface with aspatula until the benzene has evaporated. The mass obtained is heatedfor 2 hours at 150 and, after cooling again worked on glass with aspatula. The product obtained, which is a soft grease which can beworked up well, has the following lubricating properties:

Penetration (in tenths of a millimeter):

ASTM D1403-56T (year 1958)- Unworked 281 Worked 298 Drop point:

ASTM D566-42 (year 1957)- Worked: above 238 (I.P. 132/57) Example 4 97.5parts of 2,4,6-tris-dihexylamino-1,3,5-triazine, 1.5

parts of dibutyl phosphite and 1 part of phenyl-a-naphthylamine aremixed well by stirring. Compared with the pure triazine, the mixtureformed has improved sta bility to oxidation and better load carryingproperty.

Similar results are obtained if anticorrosives suitable for the intendeduse are added in amounts of 0.01 to 2% of the2,4,6-tris-dibutylamino-1,3,5-triazine.

Example 5 99.8 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 0.2part of benzotriazole are mixed. Compared with the pure triazine, themixture obtained has a less corrosive action in particular on copper andalloys thereof.

Example 6 sired solution in the triazine derivative.

Example 7 Oxidation and corrosion test on2,4,6-tris-dibutylaminos-triazine.

To make this test, 100 parts by volume (88 parts by Weight) of theproduct are heated for 6 hours at 260, 5000 parts by volume of air perhour being simultaneously bubbled through the liquid. Two pieces of mildsteel are suspended in this liquid. The metal attack is expressed inmg./sq. cm. The change in viscosity during the heating is measured at37.8 and is given in percent The acid formation during the test isexpressed in mg. KOH/g.; the sludge formation in mg./100 parts by volumeof product.

(a) '100 parts by volume of 2,4,6-tris-dibutylamino-striaz'ine withoutany additives at all showed a change in viscosity of 16.8%, acid content3.42, sludge 43, metal attack 0.05.

(b) 100 parts by volume of 2,4,6-tIis-dibutylamino-striazine, plus 1% ofTopanol CA, a commercial product 10 ofImperial Chemical Industries, acompound ot a sterically hindered phenol type, showed a change inviscosity of 13.0%, acid content 2.90, sludge 13, metal attack 0.08. (c)100 parts of 2,4,6-tris-dibutylamino-s-triazine plus 1% by weight ofdidodecyl selenide showed a viscosity change of 8.19%, acid content0.32, sludge 13, metal attack 0.08.

' Example 8 70 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and partsof sebacic acid di-2-ethyl-hexanol ester are stirred together. Themixture has a viscosity of 50.1 centistokes at 37.8 and 7.5 centistokesat 98.8". ASTM slope 0.68.

Example 9 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 50 partsof the triester of pelargonic acid and 1,1,1-trimethylolpropane arestirred together. This mixture has a viscosity of 48.1 centistokes at378 and 7.2 centistokes at 988. ASTM slope 0.70.

Example 10 At 98.8=17.33 centistokes At 37.8=42.24 centistokes Example11 50 parts of 2,4,6-tris-dibutylamino-1,3,5-triazine and 50 parts ofmineral oil SA'E-IO are stirred together.. This mixture has a viscosityof 75.66 centistokes at 37.8 and 8.82 centistokes at 988. ASTM slope0.71.

The following Table I shows the physical data of the compounds fromwhich the suitability of these stable, difiicultly volatile melaminederivatives as hydraulic liquids and/or lubricants can be seen. Columns2 and 3 give the viscosity measured at F. (=37.8 C.) and 210 F. (989C.), and column 4 shows the so-called ASTM slope.

The meaning of the ASTM slope is as follows: If in a co-ordinate system,the temperature (in degrees Fahrenheit) is given as the abscissa and thenatural log'of the viscosity (in centistokes) is given as ordinate, thena plotted curve is obtained which, for practical purposes, can beregarded as a straight line. Thus the viscosity for the wholetemperature range can be interpolated from two points determinedexperimentally (conventionally the viscosities at 100 F. and 210 F. aredetermined). The slope of this line is a standard for the dependency ofthe viscosity on temperature. Therefore, the ASTM slope is the quotientof the ordinate over the abscissa of the two points measured in cm.which are obtained by plot-ting the actual viscosity values at varioustemperatures in the ASTM chart. The ASTM Standard Viscosity-TemperatureCharts for Liquid Petroleum Products (Method D 341) are standard graphswhich closely resemble the coordinate system described above.

The lower the figure shown for a liquid in this ASTM slope the bettersuited it is as lubricant. A value of over 1.0 means that the liquid inquestion is not very suitable. ASTM is an abbreviation for AmericanSociety for Testing Materials, 1916 Race Street, Philadelphia, -Pa.,U.S.A.

Columns 5 and 6 show the loss in weight in percentage within 6' hoursincurred by a sample of 25 ml. when heated -to 380 or 400 C. in a glasstest tube of about 25 mm. diameter with simultaneous introduction ofnitrogen (2 liter per hour).

Column 7 shows the alteration in the viscosity in percentage measured at210 F. incurred by the sample when heated for 6 hours as describedabove.

TABLE 1 Viscosity in centistokes Loss in weight after Change in at- 6hours at viscosity after Compound ASTM 6 hours in slope centistokes 100F. 210 F C. Percent in percent (318 C.) (98.8" C at 210 F.

2,4,6-trisdibutylamino1,3,5-triazine 131. 2 12. 69 0. 100 380 6. 59 -13.3 2,4,6-trisdihexylammo-1,3,a-triaz1ne 12s. a 13. 83 0. e50 400 m 8 Thelubricity of representative lubricants according to the first aspect ofthe invention as compared with the luhricity of di-3,5,5-trimethyl-hexylsebacate and several 15 commercial lubricants was measured in a Shellfour-ball apparatus. The apparatus was run for 30 minutes at 1420revolutions per minute under a 40 kg. load and using half-inch Grade AS.K.F. steel balls. The starting temperature was about 40 C. The resultsare summarized in the following Table 11:

TABLE II 7 Substance used: Scar diameter in mm.

2,4,6 tris-di-b utylamino-d,3,5 triazine 0.452Trimethylolpropane-tripelargonate 0.768Di-3,5,5-trimethyl-hexyl-sehacate 0.896 Di-Z-ethyl-hexyl-sebacate 0.850Di-Z-ethyl-hexyl-adipate 0.915 Methyl phenyl silicone (MS 550 of theMiddland Silicone Ltd.) 1.93 Mineral oil (Mobil DTE light) 0.898

Each of the values given aboveis the average from three measurements.

As'can be seen from the above Table II, the compounds according to theinvention can be used directly for the lubrication of solid surfaces.

Example Z2.2-diethylamino-4-dibzerylamino-d-dodeq l- A mixtureconsisting of 157 parts of 2-diethylamino-4-.dibutylamino-fi-chloro-s-triazine, 115 parts of dodecylamine and 31.2parts of pulverized sodium hydroxide are carefully heated at 100 whilestirring. The whole is then stirred for 5 hours at 120, diluted with 170parts of a mixture of xylene water and refluxed for another 4 hours.Sodium chloride and excess sodium hydroxide are then removed byfiltration and the filtrate is washed with water and then distilled.After distilling off the xylene, the residue is distilled in a highvacuum. At 205207 under 0.02 torr, 208 parts of a thinly liquid mass areobtained. Its refraction index is 22 14980 and at 30 to 40 it is stillclear and flowing.

Analysis.C H N M3 17. 462; calculated: C 70.10% H 11.70%, N 18.20%.Found: C 69.99%, H 11.51%, N 18.73%.

The same end product is also obtained if, instead of sodium hydroxide,potassium hydroxide or a mixture of these two hydroxides is used. Agreat excess of dodecylamine can replace the sodium hydroxide.

Because it is still a clear, flowing liquid at 30 to -40, and because ofits slight volatility, its very high boiling point and its great thermalstability, this compound either alone or combined with analogouscompounds having similar properties. is suitable as a hydraulic liquidand as lubricant under extreme conditions, for example in aero engines.

Example ]3.2-diezhylamino-4-dibutylamirw-6-octadecylamino-s-triazine NHCrsHs? a e C 4 10 N C 2115 K 9 4 N C 2115 A mixture consisting of 119parts of 2-diethylamino-4- dibutylamino-6-chloro-s-triazine (B3 to" 138,n 1.5142), 112 parts of octadecylarnine and 20 parts of pulverizedsodium hydroxide is stirred for 1 hour at and for 4 /2 hours at Themixture is then diluted with 170 parts of xylene and stirred for another6 hours under reflux. After removing precipitated matter by liltrationand washing the filtrate with water, the solvent and excess amine arefractionally distilled at a pressure of 0.2 torr and then heated foranother hour at 240 bath temperature under 0.02 torr. The residue, 194parts, is a colorless oil having a refraction index n =1.5055; itcrystallizes at 30. The yield is 93.5% of the theoretical.

Analysis.C l-I N calculated: C 72.7%, H 12.10%, N 15.49%. Found: C72.96%, H 12.31%, N 15.22%.

This melamine derivative is very thermostable; it is also only slightlyvolatile at very high temperatures; it is very viscous and the viscosityhas only a relatively slight dependeuce upon the temperature. Forexample, the viscosity measured at 98.8, after 6 hours heating at 380",only changes by 0.7%. Because of these properties this compound is anexcellent lubricant.

Example I4.-2,4-bis-dibuiylam inc-6J2examethylcneimino-s-triazine Amixture consisting of 109.5 parts of2,4-bis-dibutylamino-6-chloro-s-triazine, 39.6 parts ofhexamethyleneimine and 15.2 parts of pulverized sodium hydroxide isstirred while cooling. Alter a half hour it is heated to 120, parts ofxylene are added and the Whole is stirred for another 9 hours at thistemperature. The usual working up and distillation produced 121 parts ofa colorless oil, the main fraction boiling at 178-180 under 0.002 torr.Refraction index: 12 15123; yield: 93.5% of the theoretical.

Analysis.C H' N M.W. 432; calculated: C 69.5%, H 11.12%, N 19.44%.Found: C 69.73%, H 11.23%,

Example 15 45 parts of 2,4-bis-(di-n-butylamino)-6-piperidin0-1,3,-t'riazine (Table III, No. 10) having a viscosity of 15.17 centistokesat 98.8- and 55 parts of a highly purified mineral oil (Regal Oil B) arestirred together. The mixture has the good lubricating properties of thecomponents and the viscosity of the mixture is 7.32 centistokes at 98.8.

The application range of the melamine compoundused is considerablybroadened by this reduction of the viscosity in that, for example, themixture can be used, eg as power transmitting agent in parts of machineswhich are temporarily exposed to temperatures which are lower than usualworking temperatures. Under such conditions, the melamine derivativealone is less suitable for use.

Lubricant compositions having an extended range of uses are obtained inthe same manner with melamine derivatives of relatively high viscositysuch as, e.g., the compounds Nos. 8, 12, 13, 14, 15, 16, 17, 18, 22, 23,24,25 and 27 in Table III by mixing them in any ratio desired accordingto the intended use with Regal Oil B.

Example 16 80 parts of2-diethylamino-4-di-n-butylamino-6-dihexylamino-1,3,5-triazine (TableIII, No. 13) and 20 parts of sebacic acid di-Z-ethylhexanol ester. Themixture has the good lubricant properties of the components and aviscosity of 0.713 centistoke in comparison to 9.98 centistokes at 98.8of the melamine derivative used alone.

When the viscosity is reduced "by mixing with synthetic lubricants of anester basis the application range of melamine derivatives useableaccording to the invention is broadened in that such mixtures can beused, e.g. as

power transmission agents, in machines Which are tem- Example 17 87.4parts of 2,4-bis-diethylamino-6-ditetradecylamino- 1,3,5-triazine (TableIII, No. 17) and 12.6 parts of a methylphenyl silicone (MS 550 producedby Midland Silicones Ltd.) are homogeneously mixed by stirring.

. The mixture is a lubricating oil having an excellent ASTM slope of0.608.

The silicone oil MS 550 is characterized by the following viscosities:

Centistokes At 98.8 19.6 At 37.8" 78.34

In the same way, lubricant compositions having a ratio of components asdesired and having viscosity properties desired for the intended use canbe produced with the other melamine derivatives given in Table I andsilicone oils.

Example 18 6.5 parts of 2,4-bis-dibutylamino-6-ditetradecylamino-1,3,5-triazine (Table III, No. '18) are stirred with 35 parts of sebacicacid di-Z-ethyl-hexanol ester. This mixture has a viscosity of 46.90centistokes at 37.8 and 7.74 centistokes at 98.8. ASTM slope 0.64.

If, in the above example, instead of 35 parts of sebacic aciddi-Z-ethyl-hexanol ester, 35 parts of dinonyl adipate are used, then amixture is obtained which has a viscosity of 49.36 centistokes at 37.8and 7.95 centistokes a 98.8. ASTM slope: 0.66.

Example 19 60 parts of 2,4-bis-dibutylamino-6-ditetradecylamino-1,3,5-triazine (Table III, N0. 18) and 40 parts of the triester ofcaprylic acid and 1,1,1-trimethylol propane are stirred together. Thismixture has a viscosity of 51.86 centistokes at 988 and 8.13 centistokesat 98.8. ASTM slope: 0.66.

Example 20 55 parts of 2,4-bis-dibutylamino-6-ditetradecylamino-1,3,5-triazine (Table III, No. 1 8) are stirred with 45 parts of thetriester of pelargonic acid and 1,1,1-trimethylolpropane. This mixturehas a viscosity of 53.21 centistokes at 378 and 8.32 centistokes at98.8. ASTM slope: 0.66.

Example 21 The mass obtained is heated for 45 minutes at I and, aftercooling, is again worked with a spatula.

A good grease which can be well worked up is obtained. Similar resultsare obtained by using the melamine derivatives given in Table III withthe addition of the usual thickeners employed for the particularpurpose.

Example 22 99 parts ofZ-diethylamino-4-dibutylamino-6-dihexylamino-l,3,5-triaziue (Table III,No. 13) and 1 part of iminodibenzyl are stirred together until thelatter has completely dissolved. The mixture obtained has improvedstability to oxidation compared with the pure triazine compound.

Similar results are obtained if antioxidants suitable for the intendeduse are added in amounts of .01 to 5% to the compound given in TableIII. As antioxidants may also be used didodecyl selenide or 1,1,3-tris(4'-hydroxy-5'- tert-butyl-2-methylphenyl -butane.

Similar results are obtained if the compounds given in Table III aremixed with high pressure additives and antioxidants suitable for theintended use in amounts of 0.01 to 5%.

Example 23 97.5 parts of 2,4-bis-dibutylamino-6-ditetradecylamino-1,3,5-triazine (Table III, No. 1), 1.5 parts of dibutyl phosphite andone part of phenyl-a-naphthylamine are mixed well by stirring. ComparedWith the pure triazine, the mixture formed has improved stability tooxidation and better load carrying property. I

Similar results are obtained if anticorrosives suitable for the intendeduse are added in amounts of 0.01 to 2% to the compounds given in TableIII.

lonite as purifying agent.

Example 24 99.8 pants of 2,4-bis-dibutylamino-6-ditetnadecylamino1,3,5-triazine (Table III, No. 18) and 0.2 part of benzotriazole aremixed. Compared with the pure triazine, the mixture obtained has a lesscorrosive action, particularly on copper and alloys thereof.

Example 25 1250 parts of 2,4-bis-dibutylamino-6-chloro-s-triazine and1490 parts of amine Armeen 2C (composition given below) are stirred in a5 liter round glass under an atmosphere of nitrogen. 150 parts ofpulverized sodium hydroxide are added. Due to the exothermic reaction,the temperatures rises to 135. The Whole is then stirred at 130 bathtemperature for hours, then washed with water at 90 until the pH is 7-8and it is free of chlorine ions, after which it is filtered cold. Yield87% In the preceding example, the filtrate contains 0.3% of secondaryand primary amines and 1.65% of tertiary amines. The composition of thefiltrate depends upon the composition of the amine mixture used, and maybe free from primary, secondary and tertiary amines.

The amine used in this and in the following examples is a technicalproduct which consists of 85.6% secondary amines of an average molecularweight of 423, 6.6% primary amines of an average molecular weight of 220and 7.8% tertiary amines of an average molecular weight of 626.

The following alkyl radicals are present in the amine sample used, inthe following amount expressed in percent by weight: C 8%, C 9%, C 47%,C 18%, C 8%, C 10%, unsaturated alkyl 0%.

This amine mixture is referred to, hereinafter, for the sake of brevity,as Armeen 2C, under which name the same is sold.

Fromthis it can be seen that for the reaction of 35.5 parts of labilechlorine, 415.7 parts of this amine mixture are necessary. However, eachbatch of Armeen 2C must be analyzed before use because the compositionof the commercial product varies slightly. Depending on the specialpurpose, Armeen 2C can be fractionated by distillation.

Example 26 250 parts of the condensation product described. in Examplefrom 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C which, inthis case, contains 1.6% of secondary amines of average molecular weightof 423 and 1.6% of tertiary amines of average molecular weight of 626,are diluted with 750 parts of cylo-hexane and stirred in a rapidlyrotating mixing apparatus for minutes at -45 with 110 parts of anacid-pretreated montrnoril- This acid-pretreated montmorillonite is soldunder such tradenames as Tonsil AC and Celite FC. The mixture isfiltered and the filtrate is then treated again with 90 parts of TonsilAC under the same conditions and again filtered. The residualcyclohexane is removed from the filtrate by distillation and. heatingfor 1 hour at 230 under 051 torr. 217 parts of an almost colorless clearliquid are obtained, the total amine content of which is lower than0.1%, which is the sensitivity limit of the potentiometric determinationused.

The above-described purification can also be performed at a dififerenttemperature range, e.g., at 60-70 or at 20-25 Alkanes such as hexane canalso be used instead of cyclohexane. In cases in which the free aminecontent of the crude product is very low, Tonsil AC can also be usedwithout a solvent.

Example 27 parts of the condensation product described in Example 25from 2,4-bis-dibutylamino6-chloro-s-triazine and Armeen 20 whichcontains 1.2% of secondary amines (average molecular weight 423) and1.0% of tertiary amines (average molecular weight 626) are diluted with500 parts of cyclohexane and rapidly stirred with 30 parts of Celite FC(Adsorption earth, Messrs. Johns-Manville), then filtered and againtreated with fresh Celite FC until the product is free from amines. Itis also possible to remove small amounts of free amines by using thehydrogen form of organic ion exchangers such as Amberlite IR 120. Here,too, hexane and methyl-cyclohexane can be used as diluents. Sometimesthis treatment must be repeated until the end product contains no morefree amines.

Example 28 i 650 parts of the condensation product described in Example25 from 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C whichcontains 0.3% secondary amines (average molecular weight 423) and 1.6%tertiary amines (average molecular weight 626), are distilled at 0.007torr. The main fraction of 422 parts contains 0.15% of secondary aminesand 1.25% of tertiary amines. The distillate is diluted with double theamount of cyclohexane and treated three times with 42 parts of Tonsil ACeach time. Potentiometric analysis of the end product shows a totalcontent of free amines of less than 0.1%, which is the sensitivity ofthe method. The content of secondary amines, which can be determinedphotometrically, is 0.01% or less, which again corresponds to thesensitivity of the method used.

Example 29 200 parts of the condensationproduct described in Example 25from 2,4-bis-dibutylamino-6-chloro-s-triazine and Armeen 2C whichcontains 1.6% secondary amines (average molecular weight 423) and 1.6%tertiary amines (average molecular weight 626) are extracted with 50parts of acetic acid and then extracted four times, with a total of 110parts of glacial acetic acid, washed neutral with water, filtered anddried. 165.2 parts of a product are obtained which contains less than0.1% of free amine. In a similar way, the free amines which may bepresent in the triazines produced in the other examples, can beselectively extracted.

Example 30 97 parts of 2,4-bis-dibutylamino 6-di(C H )amino-1,3,5-triazine (Table III, No. 18) wherein x has a mean value of 14, and3 parts of a polymer of methacrylic acid ester, in particularpoly-Z-ethylhexyl-methacrylate (HF 825 of Messrs. Rohm & Haas Co.,Philadelphia, Pa., U.S.A.), are homogeneously mixed by stirring. Thismixture has a lower solidification point than the pure 2,4-bis-dibutylamino-6ditetradecylamino-1,3,5-triazine.

Example 31 250 parts of the condensation product of2,4-bis-diethylamino-'6-chloro-s-triazine and Armeen 2C which contains1.0% secondary amines (average molecular weight 423) and 0.9% tertiaryamines (average molecular weight 626) are diluted with 750 parts ofcyclohexane and treated with Tonsil AC (110 parts) exactly as describedin Example 26. The filtrate obtained is also treated with parts ofTonsil AC. 220.5 parts of an amine-free product are obtained. With thesame bleaching earth, other s-triazines of Table III such as, e.g. Nos.12, 16, 21, 24, 25 and 28 can be purified free of amines. Here also,hexane can be used as diluent instead of cyclohexane.

The following Tables III and IV contain data of other N,N',N-substitutedmelamines usable aCcording to the invention, which melamines fall underthe general formula They are produced by reacting cyanuric chloride insuccessive steps with the primary and secondary organic amines given inthe columns headed X, Y and Z in Table III according to the methoddescribed in detail in Example 12. Column 5 of Table HI shows the yieldattained in the last step in percentof the theoretical, columns 6 and 7give the boiling point of the compounds under reduced pressure, column 8shows the refractive index and column 9 the molecular weight of thecompounds.

Table IV shows the physical data of the compounds from which thesuitability of these stable, difficultly volatile melamine derivativesas hydraulic liquids and/ or lubricants can be seen. Columns 2 and 3give the viscosity measured at 100 F. (37.8 C.) and 210 F. (98.8 C.),and column 4 shows the so-called ASTM slope.

Columns 5 and 6 show the loss in weight in percentage Within 6 hoursincurred by a sample of 25 ml. when heated to 380 or 400 C. in a glasstest tube of about 25 mm. diameter with simultaneous introduction ofnitrogen (2 liters per hour).

Column 7 shows the alteration in the viscosity in percentagemeasured at210 F. incurred by the sample whe heated for 6 hours as described above.

TABLE III B.P. 8.12- No. X Y Z Percent 12. MW

0. Torr N(C3H5)2 N(C4H9)2 NH 0 21125 90. 0 205-7 0. 02 1. 4980 462N(CzH)z N(C4H9)2 NH 0 8E137 93. 3 220 0. 02 1. 5055 546 N(C4H9)2 N(C4H9)2 NH 031117 75. 4 208- 0. 03 1. 4969 462 4 9)2 4 9)2 H 0.21125 88. 7204- 0. 03 1. 4933 51s N(C4Ha)a N(C4Hs)2 NHCIB 37 77. 0 266- 0. 02 1.4905 G N(C4H9)2 N(C4H9)2 NH@ 92. 6 -99 0. 01 1. 5118 432 7 N(C4Hn)2N(C4Hs)2 NHCH2$HC4H0 85. 0 173-85 0. 01 1. 5000 462 8 N(C4Hn)2 N(C4Ha)zN\@ 83. 9 187-98 0. 02 1. 5083 460 /C H 9 N(C4H9)2 N(C4H9)fl N\ 88. 8186-96 0. 01 1. 4927 476 8 17 OHECHZ 10 N(C4H9)z N(C4Hn)z CH2 92. 5178-82 0. 02 1. 5112 418 0 CHQOHZ 11 N(C4Hs)z N(C4H9)2 N(CsH13)z 92. 9198-207 0. 02 1. 4921 518 /C H 12 N(C2H5)g N(CzH )z N\ 92. 3 162-670.02 1. 5023 364 CBHXT 13 N(CgH N(C4H9 )z N(CuH13)2 93. 0 202-4 '70.02 1. 4937 462 0 H 14- N(CnH5)z N(C4H9)2 N\ 91. 5 210 001 1. 4903 56012 25 CH 1 1.5". N(C4H0)2 N(C4H9)z N\ /CHz)4 93. 5 178-80 0. 002 1. 5123432 16 N(CzH )z N( 4HD)2 N( 14 2S)2 x 98. 0 220 0. 03 1. 4856 686 17N(C2H5)z N(CzH5)z N(C 4Hz9)z 93. 0 220 0. 01 1. 4867 630 18, N(C4H9)gN(C4Hp)g N(C1-1Hz9)g 94. 1 220 0. 02 1. 4855 742 /CH3 19 N\ N(CzH5)gN(C4H9)z 95. 4 161-3 0. 04 1. 4967 420 CaHn N(CzH5)2 N(C2H5)g N(CsH17)294. 5 190 0. 06 1. 4931 462 N(O2 5):; N(C2H5)3 N(C12H35)z 96. 5 200 0.02 1. 4897 574 N(C4H5)z (C4Ha)z N(CsH17)2 98.1 200 0. 07 1. 4908 574 (045)2 NECQIUQ N(C12Hz5)3 98. 0 200 0. 05 1. 4866 636 CH N O4HSJ120121125): 97. 4 200 0. 06 1. 4892 602 N(CH3)2 N(O4H9)2 N(C14H29)2 96. 7200 0. 05 1. 4876 658 N(CgH5)z N(C4H9)z N(C!H17)2 95. 3 200 0. 03 1.4924 518 N(C3H5)g N(C4Hg)g N(C1:| 25)2 94. 6 200 0. 03 1. 4872 630 CH2CE: I 28.-- N\ CHQs N(C14H29)z N 301193 97. 1 240 0. 05 1. 5000 598 C aC 2 NOTE is a mixture of straight chain alkyl groups the mean carbonnumber of which corresponds to about 14.

TABLE IV Viscosity in centistokes Loss in weight after 6 Change in athours at viscosity N0. ASTM after 6 slope hours in 100 F. I 210 F. 0.Percent centistokes I (37.8 C.) (98.8" C.) in percent at 210 F.

1 133. 7 10. 75 0. 774 380 3. 72 400 11. 97 2 158.4 13. 77 0.708 380 3.03 400 11.70 3 151.7 11.84 I O; 760 I 380 5.20 400 12.90 4 149. 12. 910. 721 380 5. 95 400 14. 10 5 192.1 15. 69 0. 698 380 4.9 400 12. 6 6989. 3 31. 25 0.760 380 2. 7 I 400 8. 4 7 282.6 14.86 0.797 380 7. 24

3 400 17. 67 8 552 24.82 0.737 380 5.33 400 12. 91 9 89. 66 I 9. 730.724 I 380 p 6.16 400 17. 8 10 280 15. 17 0. 787 380 2. 46 +4. 87 4006. 99 +15. 47 11 113. 1 12. 03 0. 687 380 6. 70 +3. 16 400 19. 04 +7. 4012 50. 23 6. 06 0. 702 380 3. 52 +5. 1, I 1 400 45. 16 +19. 8 13 95. 799. 97 I 0. 728 380 5. 27 +0. 73 400 15. 6 +6.15 14 106. 4 12.22 1 0. 667380 2. 54 3. 76 I 400 15. 3 +12. 80 15 227. 5 16. 69 0. 710 380 3; 07+6. 61 400 9. 26 +22. 90 111. 1 13. 12 0. 647- 380 5. 18 8. 07 400 19,86 +0. 53 113. 7 13. 57 0. 64 380 7. 0O 8. 28 400' 23. 78 +6. 55 128. 7815. 18 0.63 380 7. 17 +1. 19 400. 21. 88 +16. 90 64. 80 7. 47 0. 766 3804. 55 +9. 41

The lubricity of 5 representative compounds according to the secondaspect of the invention as compared with the lubricity ofdi-3,5,5-trimethyl-hexyl sebacate and several commercial lubricants wasmeasured in a Shell 4-ball apparatus. The apparatus was run for 30minutes at 1450 revolutions per minute under a 40 kg. load and usinghalf-inch Grade A S.K.F. steel balls. The starting temperature was.about 40 C. The results are summarized in the following Table: V:

* In this test lubrication ceased even after 2.5 minutes.

Each of the values given above is the average from three measurements.

As can be seen from the above table, the compounds according to thesecond aspect of the invention can be used directly for the lubricationof solid surfaces. The

following test illustrates the applicability of the lubricant mentionedfor the lubrication of glass surfaces:

When the compound No. 16 in Table III is applied to the ground glasssurface. of a stopper and the stopper is placed into the correspondinglyformed orifice of a glass flask, the stopper is held fast and the flaskis rotated around it at least 3.9 10 times at room temperature for 130hours, without sticking due to glass to glass friction. If, instead ofthe compound No. 16 of Table III, a commercially available and widelyused silicone high vacuum fat is employed under the same conditions thenthe rotated flask becomes. stuck after 24 hours.

EXAMPLE 32 88 g. ml.) of the product obtained according to Example 26,first paragraph, which was hydrogenated cold with H over palladium toremove any residual olefinic double bonds, is heated to 260 for 6 hours.At the same time, 5000 parts by volume of air per hour are passedthrough the liquid. The degree by which the metal is attacked isexpressed in mg./cm. The change of viscosity which occurs during theheating is measured at 38.0 and given in percentage. The acid thusformed is measured at the end of the experiment and expressed in mg.KOH/g. The formation of sludge, i.e., the undissolved matter dispersedin the liquid reaction mixture, is determined by filtration and weighPercent Change in viscosity +16.0 Acid concentration 5.06 Sludge 11.4Metal attack 0.08 Varnish Very heavy (a) 88 g. (100 ml.) of the productobtained according to Example 26, first paragraph, which washydrogenated cold with H over palladium to remove any residual olefinicdouble bonds, was mixed with 1 g. of 1,1,3-tri- (2' methyl 4hydroxy-S'-tert-butylphenyl) butane and further treated as describedabove. The resulting product alforded the following data in the abovetest:

Percent Change in viscosity +6.4 Acid concentration 0.45 Sludge 8.8Metal attack 0.06

Varnish Moderate (b) 88 g. (100 ml.) of the product obtained accordingto Example 26, first paragraph and 1 g. of2,6-di-(tertbutyl)-4-methyl-l-hydroxy-benzene treated as describedabove, afforded the following data in the above test:

Percent Change in viscosity +5.6 Acid concentration 0.55

Sludge 20.1 Metal attack 0.13

Varnish Slight (c) 88 g. (100 ml.) of the product obtained according toExample 26, first paragraph, and 1 g. of 2tert-octyliminodibenzyltreated as described above, afforded the following values in the abovetest:

amino-s-triazine A mixture consisting of 148 parts of2,4-bis-dibutylamino-6-chloro-s-triazine, 129 parts ofp-phenoxyaminobenzene and 16 parts of pulverized sodium hydroxide isheated while stirring for hours at 150 and then for 3 hours 45 minutesat 165. The inorganic components are removed by filtration and thefiltrate is fractionally distilled in vacuo. The desired triazinederivative distills at 22 B.P. 240 under 0.02 torr (bath temperature280-290) without decomposition as a highly viscous liquid.

Yield: 93.4% of the theoretical.

Analysis.C H N O, 71.75%, H, 8.88%, N, 1623. 8.82%, N, 1636.

Because of its very good thermostability, its slight vo latility whichin a test showed that under introduction'of nitrogen at atmosphericpressure for 6 hours at 400, a loss of weight of only 2.7% occurred, asWell as its high viscosity, the compound is avaluable lubricant forparts of machines working at high temperatures.

calculated: C, Found: C, 71.76%, H,

Example 34.-2,4-bis-dibu tylamino-6-p-tert-butylphenylamino-s-triazine Amixture consisting of 148 parts of2,4-bis-dibutylamino-6-chloro-s-triazine, parts of p-tert-butylanilineand 16 parts of pulverized sodium hydroxide is heated while stirring for15 minutes at 100 and then for 8 hours at The mixture -is then dilutedwith xylene, the inorganic components are removed by filtration, thefiltrate is washed with water, dried and distilled. At B.P. of 224232and 0.1 torr, 179- parts of a colorless oil distill.

Refraction index n 1.5432; yield 97.1% of the theoretical.

Analysis.C I-I N calculated: C 72.30%, H 10.37%, N 17.43%. Found: C72.46%, H 10.46%, N 17.47%.

Because of the very good thermostability of the compound, its slightvolatility which is shown by the loss in weight which, ontheintroduction of nitrogen at atmospheric pressure for 6 hours at 400, isonly 10%, and because of its favorable medium viscosity and the onlyslight alteration thereof which occurs on heating, this melaminederivative is a suitable turbine oil for gas turbines.

Example 35 3 parts of copper phthalocyanine are stirred in 25 parts byvolume of benzene in an Ultraturax mixing apparatus (Janke & Kunkel,Staulfen, Baden, Germany). 9 parts of 2,4 bis dibutylamino 6 ptertbutyl-phenylamino-1,3,5-triazine are slowly added to this mixture andthe whole is then stirred for 45 minutes. The homogenous mass soobtained is worked on a glass surface With a spatula until the excessbenzene has evaporated.

The mass obtained is heated for 45 minutes at and, after cooling, isagain worked With a spatula.

A good grease which can be well worked up is obtained.

Similar results are obtained when using the melamine derivatives givenin Table VI with the addition of the usual thickeners employed forparticular purposes.

Example 36 99 parts of2,4-bis-dibutylamino-6-(N-methyl-N-phenylamino)-1,3,5-triazine and 1part of i-minodibenzyl are stirred together until the latter hascompletely dissolved. The mixture obtained has improved stability tooxidation compared with the pure triazine compound.

Similar results are obtained if antioxidants suitable for the intendeduse are added in amounts of 0.01 to 5% to the compounds given in TableVI. As antioxidants may also be used didodecyl selenide or Topanol CA ofthe Imperial Chemical Company.

Similar results are obtained if the compounds given in Table VI aremixed with high pressure additives and antioxidants suitable for theintended use in amounts of 0.01 to Example 37 Example 38 99.8 parts of2,4-bis-dibutylamino-6-p-phenoxy-phenylamino-1,3,5-triazine and 0.2 partof benzotriazole are mixed. Compared with the pure triazine, the mixtureobtained has a less corrosive action, particularly on copper and alloysthereof.

Example 39 97 parts of 2,4-bis-dibutylamino-6-benzylamino-1,3,5-triazine and 3 parts of polymers of methacrylic acid ester, inparticular poly-2-ethylhexyl-methacrylate (HP 825, Rdhrn and Haas Co.,Philadelphia, Pa.) are homogeneously mixed by stirring. This mixture hasa lower solidification point than the pure 2,4-bis-dibutylamino-6-benzylamino-l,3,5-triazine.

The choice of polymers as additives to reduce the solidification pointis advantageously made according to the desired solution in the triazinederivative.

24 The following Tables VI andVlI contain examples of N,N,N-substitutedmelamines of the formula A.) z usable according to the third. aspect ofthe invention. They are produced by reacting cyanuric chloride insuccessive steps with the primary and secondary organic aminescorresponding to X, Y and Z according to the method described in detailin Example 33. Column 5 of Table VI shows the yield attained in the laststep in percentage of the theoretical, columns 6 and 7 give the boilingpoint of the compounds under reduced pressure, column 8 shows therefraction index and column 9 the molecular weight of the compounds.Column 2 in Table VII contains the formulas of the compounds and column3 and the following columns show the results of elementary analysis forcarbon, hydrogen and nitrogen expressed in percent as compared with thetheoretical content.

Table VIII shows the physical data of the compounds from which thesuitability of these stable, difiioultly volatile melamine derivativesas hydraulic fluids and/ or lubricants can be seen. Columns 2 and 3 givethe viscosity measured at 100 F. (37.8" C.) and 210 F. (98.8 C.), andcolumn 4 shows the so-called ASTM slope.

Columns 5 and 6 show the loss in weight in percentage within 6 hoursincurred by a sample of 25 ml. when heated to 380 or 400 C. in a glasstest tube of about 25 mm. diameter with simultaneous introduction ofnitrogen (2 liters per hour).

Column 7 shows the alteration in the viscosity in percentage measured at210 F. incurred by the sample when heated for 6 hours as describedabove.

TABLE'VI BPat- No. X Y Z Percent 11- MW O. Torr 1 M 2 5 M61 5): NHCHFQ85.5 180-88 0.01 1.5582 328 2 N(C4Ho)z N(C4H0)2 mom-Q 85.0 206-25 0.071.5323 440 a morn): molar): NHO 03.4 240 0.02 1.5500 518 4 on; 4 moan):worm); NH(ECH0 07.1 224-32 0.1 1. 5432 482 o2r15 5 N(C4H0)2 N(C4Hg)z N\@906 104-00 0.00 1.5273 454 TABLE VII Analysis, percent Empirical No.Formula C H N Cale. Found Cale. Found Gale. Found s5. s0 s5. s5 8. 55 s.25. e0 25. 52 70. 9 7o. 9 10. o 10. 14 19. 1 19. 40 71. 75 71. 70 8.88s. 32 10. 2s 10. 3s 72. 3 72. 40 10. 37 10. 17. 43 11. 47 71. 42 71. 251o. 12 0. 27 1s. 40 1s. 00

TABLE VIII Viscosity in centistokes Loss in weight after 6 Change inathours viscosity No. ASTM after 6 slope hours in 100 F. 210 F. 0.Percent centistokes (37.8 C.) (98.8 C.) in percent at 210 F.

The lubricity of a representative lubricant according to the inventionwas measured in a Shell four-ball apparatus. The apparatus was run for30 minutes at 1450 revolutions per minute under a 40 kg. load and usinghalf-inch Grade A S.K.F. steel balls. The starting temperature was about40 C.

The compounds according to the invention can be used directly for thelubrication of solid surfaces.

Example 40 50 parts of2,4-bis-dibutylamino-fi-p-phenoxy-phenylamino-1,3,5-triazine and 50parts of dinonyl adipate are stirred together. This mixture has aviscosity of 95.0 centistokes at 37.8 and 9.5 centistokes at 988. ASTMslope 0.74.

Example 41 50 parts of2,4-bis-dibutylamino-6-(N-ethyl-N-phenylamino)-1,3,5-tn'azine and 50parts of silicone oil DC are stirred together. The mixture has aviscosity of 85.2 centistokes at 37.8 and 16.3 centistokes at 98.8".ASTM slope 0.50.

The silicone oil DC of Dow Corning Co. has the following viscosityvalues:

Centistokes We claim:

1. A lubricant composition consisting essentially of about to 90% byweight of a compound of the formula wherein each R is an identical loweralkyl group with from 4 to 6 carbon atoms and wherein the aforesaidcompound is the essential lubricant in said composition and about 90 to10% by weight of a lubricant selected from the group consisting ofmineral oil, methyl phenyl silicone and the sebacic, valeric, caprylic,adipic and pclargonic acid esters of octyl and nonyl alcohols,pentaerythritol and trimethylolpropane.

2. A lubricant composition consisting essentially of about 55 to 90% byweight of a compound of the formula wherein each R is an identical loweralkyl group with from 4 to 6 carbon atoms and wherein the aforesaidcompound is the essential lubricant in said composition, and from about45 to 10% by weight of phthalocyanine.

3. A lubricant composition consisting essentially of a compound of theformula wherein each R is an identical lower alkyl group with from 4 to6 carbon atoms, and correspondingly from 5 to 1% by weight, calculatedon the total weight of the composition, of apoly-2-lower-alkyl-hexyl-meth acrylate.

5. A lubricant composition consisting essentially of a compound of theformula wherein each R is an identical alkyl group with from 4 to 6carbon atoms and from about 0.01 to 5% by weight, calculated on thetotal weight of the composition, of

7 didodecylselenide.

about to 99% by weight of a compound of the formula wherein X is adi-(lower' alkyl)-amino in which each alkyl radical has from 1 to 4carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to4 carbon atoms,

R, is a member selected from the group consisting of hydrogen and alkylof maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6and maximally 18 carbon atoms and cyclohexyl, the sum of the carbonatoms of R and R 9 when separate substituents being at least 8 and notmore than 28,

R and R when taken together with the nitrogen atom to which they arelinked represent a member selected from the group consisting ofpiperidino and hexa-methyleneimino;

the balance of said composition consisting of a poly-2- loweralkyl-hexyl-rnethacrylate.

7. A lubricant composition consisting essentially of a compound of theformula wherein X is a di-(lower alkyl)-amino in which each alkylradical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to4 carbon atoms,

R; is a member selected from the group consisting of hydrogen and alkylof maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6and maximally 18 carbon atoms and cyclohexyl, the sum of the carbonatoms of R and R when separate substituents being at least 8 and notmore than 28,

R and R when taken together with the nitrogen atom to which they arelinked represent a member selected from the group consisting ofpiperidino and hexa-rnethyleneimino;

and of from about 0.01 to by weight, calculated on the total weight ofthe composition, of a member selected from the group consisting ofdidodecylselenide, 1,1,3-tri-(2'-methyl-4'-hydroxy-5-tert-butylphenyl)-butane, 2,6-di- (tert-butyl)4methyl 1 hydroxybenzene, Z-tert-octylimino-dibenzyl and5-ethyl-10,10-diphenyl-phenosilazine. 8. A lubricant compositionconsisting essentially of about 10 to 90% by weight of a compound of theformula wherein R is a member selected from the group consisting ofhydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6and maximally 18 carbon atoms and cyclohexyl, the sum of the carbonatoms of R and R when separate substituents being at least 8 and notmore than 28,

R and R when taken together with the nitrogen atom to which they arelinked represent a member selected from the group consisting ofpiperidino and hexamethyleneimino;

the balance of said composition consisting of a lubricant selected fromthe group consisting of mineral oil and a synthetic ester lubricant.

9. A thickened lubricant composition consisting essentially of about 55to by weight of a compound of the formula X is a di-(lower aIkyD-aminoin which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to4 carbon atoms,

R is a member selected from the group consisting of hydrogen and alkylof maximally 14 carbon atoms, R is a member selected from the groupconsisting of alkyl of at least 6 and maximally 18 carbon atoms andcyclohexyl, the sum of the carbon atoms of R and R when tially of about55 to 90% by weight of a compound of the formula wherein X is adi-(lower alkyl)-amino in which each alkyl radical has from 1 to 4carbon atoms,

Y is a di-(lower alky1)-amino in which each alkyl radical has from 1 to4 carbon atoms, R is a member selected from the group consisting ofhydrogen and alkyl of maximally 14 carbon atoms, R is a member selectedfrom the group consisting of alkyl of at least 6 and maximally 18 carbonatoms and cyclohexyl, the sum of the carbon atoms of R and R whenseparate substituents being at least 8 and not more than 28,

R and R when taken togetherwith the nitrogen atom to which they arelinked represent a member selected from the group consisted ofpiperidino and hexamethyleneimino',

and the balance of said composition consisting of a thickener selectedfrom the group consisting of metal soaps,

bentonites, phthalocyanine pigments and violanthrone pigments.

, v 29 Q 11. A lubricant composition consisting essentially of about to90% by weight of a compound of the formula wherein X is a di-(loweralkyD-amino in which each alkyl radical has from 1 to 4 carbon atoms,

Y is a di-(lower alkyl)-amino in which each alkyl radical has from 1 to4 carbon atoms,

R is a member selected from the group consisting of hydrogen and alkylofmaximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6and maximally 18 carbon atoms and cyclohexyl, the sum of the carbonatoms of R and R when separate substituents being at least 8 and notmore than 28,

R and R when taken together with the nitrogen atom to which they arelinked represent a member selected from the group consisting ofpiperidino and hexamethyleneimino;

and the balance of said composition consisting of a methyl 7 phenylsilicone.

12. A lubricant. composition consisting essentially of about 95 to 99%by weight of a compound of the formula wherein X is a di-(loweralkyl)-amino group in which each alkyl radical has from 2 to 4 carbonatoms, Y is a di-(lower alkyl)-amino group in which each alkyl radicalhas from 2 to 4 carbon atoms, R is a member selected from the groupconsisting of hydrogen and lower alkyl of maximally 4 carbon atoms,

R is a member selected from the group consisting of benzyl, phenyl,alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenylwherein alkoxy has maximally 4 carbon atoms and phenoxy-phenyl,

and correspondingly, from 5 to 1% by weight, calculated on the totalweight of the composition, of a poly Z-lower alkylhexyl-methacrylate.

13'. A lubricant composition consisting essentially of a compound of theformula wherein X is a di-(lower alkyl)-amino group in which each alkylradical has from 2 to 4 carbon atoms,

Y is a di-(lowe-r alkyl)-amino group in which each alkyl radical hasfrom 2 to 4 carbon atoms,

R is a member selected from the group consisting of hydrogen and loweralkyl of maximally 4 carbon atoms, R is a member selected from the groupconsisting of benzyl, phenyl, alkylphenyl wherein alkyl has maximally 12carbon atoms, alkoxy-phenyl wherein alkoxy has maximally 4 carbon atomsand phenoxy-phenyl, and from about 0.01 to 5% by weight, calculated onthe total weight of the composition, of didodecylselenide.

14. A lubricant composition consisting essentially of about 1 0 to 90%by weight of a compound of the formula N Yea wherein X is a di-(loweralkyl)-amino group in which each alkyl and correspondingly, about 90 to10% by weight, calculated on the total weight, of a lubricant selectedfrom the group consisting of mineral oil, methyl phen'yl silicone,

, the sebaci-c and adipic acid esters of octyl and nonyl alcohols.

15. A lubricant composition comprising as lubricant at least 10% of (a)a melamine derivativeselected from the group consisting of the compoundsof the formulas each R is an identical lower alkyl group of from 4 to 6carbon atoms,

each of X and X is di-lower alkyl-amino in which each alkyl has from 1to 4 carbon atoms,

each of Yand Y is di-lower alkyl-amino in which each alkyl has from 1 to4 carbon atoms,

each of R and R is a member selected from the group consisting ofhydrogen and alkyl of maximally 14 carbon atoms,

R is a member selected from the group consisting of alkyl of at least 6and maximally 18 carbon atoms and cyclohexyl, the sum of the carbonatoms of R and R when separate substituents being at least 8 and notmore than 28,

R and R when taken together with the nitrogen atom to which they arelinked represent a member selected from the group consisting ofpiperidino and hexamethyleneimino, and

R is a member selected from the group consisting of benzyl, phenyl,alkylphenyl wherein alkyl has maximally 12 carbon atoms, alkoxy-phenylwherein alkoxy has maximally 4 carbon atoms and phenoxyphenyl, and thebalance of said composition consists essentially of at least one memberselected from the group consisting of (b) from about to 10% by weight ofa lubricant selected from the group consisting of mineral oil, syntheticester lubricant, and methyl phenyl silicon, (c) from 45 to 10% by weightof a pigmen selected from the group consisting of phthalocyanine pigmentand violanthrone pigment, (d) from about 0.01% to of an antioxidant,(e)from about 0.1 to 5% of poly-(2-lower alkyl-hexyl methacrylate), (f)from to 45% of metal soap, (g)frorn 10 to 45% of bentonite, (h) from0.01 to 5% of high pressure addi tive, (i) from 0.01 to 2% ofanticorrosive. 16. A lubricant composition consisting essentially ofabout 95 to 99% by weight of a compound of the formula andcorrespondingly from 5 to 1% of a poly-2-lower alkyl-hexyl-methacrylate.

17. A lubricant composition consisting essentially of about 95 to 99% byweight of a compound of the formula 11 4) 2-N-O C N and correspondinglyfrom 5 to 1% of a poly-Z-lower alkyl-hexyl-metl'lacrylate.

18. A lubricant composition consisting essentially of about 95 to 99% byweight of a compound of the formula and correspondingly from 5 to 1% ofa poly-Z-ldwer alkyl-hexyl-methacrylate.

19. A lubricant composition consisting essentially of about 95 to 99% byweight of a compound of the formula and correspondingly from 5 to 1% ofa poly-2-lower a1kyl-hexyl-methacrylate.

20. A lubricant composition consisting essentially of a compound of theformula and from about 0.01 to 5% by weight, calculated on the 401131Wfiight 0f composition, of didodecylselenide.

21. A lubricant composition consisting essentially of a compound of theformula N C 2H5 and from about 0.01 to 5% by weight, calculated on thetotal weight of the composition, of didodecylselenide.

22. A lubricant composition consisting essentially of a compound of theformula and from about 0.01 to 5% by Weight, calculated on the totalWeight on the composition of didodecylselenide.

23. A lubricant composition consisting essentially of a compound of theformula IYK 2115):

and from about 0.01 to 5% by weight, calculated on the total weight ofthe composition, of didodecylselenide.

24. A lubricant composition consisting essentially of about 10 to byweight of a compound of the formula and correspondingly about 90 to 10%by weight of a lubricant selected from the group consisting of mineraloil, methylphenylsilicone, the sebacic and adipic acid, esters of octyland nonyl alcohols.

25. A lubricant composition consisting essentially of about 10 to 90% byweight of a compound of the formula CzHs I g Q- -Q and correspondinglyabout 90 to 10% by weight of a lubricant selected from the groupconsisting of mineral oil, methylphenylsilicone, the sebacic and adipicacid esters of octyl and nonyl alcohols.

27. A lubricant composition consisting essentially of oil,methylphenylsilicone, the sebacic and adipic acid about 10 to 90% byweight of a compound of the formula. esters of octyl and nonyl alcohols.

ITHCZHQ References Cited by the Examiner N N UNITED STATES PATENTS l H2,714,057 7/1955 Chenicek 252 -50 (H5O:)2NG\ 2,984,624 5/1961 Halter etal. 252-28 and correspondingly about 90 to 10% by Weight of a 10 DANIELE'WYMANPrimary Examiner lubricant selected from the group consisting ofmineral I. VAUGHN, Assistant Examiner.

15. A LUBRICANT COMPOSITION COMPRISING AS LUBRICANT AT LEAST 10% OF (A)A MELAMINE DERIVATIVE SELECTED FROM THE GROUP CONSISTING OF THECOMPOUNDS OF THE FORMULA